New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

Abstract

Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A – C (1 – 3), together with fourteen known compounds (4 – 17), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1 – 3 were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC₅₀ values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1 and 14 showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1 – 3 and 14 showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1 showed weak antibacterial activity against Escherichia coli.

Key words

Trichocomaceae - Talaromyces - Talaromyces trachyspermus - pyrrolobenzoxazine - talatrachyoxazine - cytotoxicity

Publication History

Received: 27 April 2020

Accepted after revision: 06 February 2021

Article published online:
05 March 2021

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